1,3-Dichloroacetone → 2-Acetoxymethyl-4-chloromethyl-4-hydroxythiazoline

HRID 1736658Notes

Reaction equation

HRID 1736658 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH2:8])=[S:7])(=[O:3])[CH3:2].[Cl:9][CH2:10][C:11]([CH2:13]Cl)=[O:12].C(=O)(O)[O-].[Na+]>ClCCCl>[C:1]([O:4][CH2:5][C:6]1[S:7][CH2:13][C:11]([CH2:10][Cl:9])([OH:12])[N:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 11018908Carbamothioylmethyl acetate

Product 1

HCID 117908272-Acetoxymethyl-4-chloromethyl-4-hydroxythiazolineYield 92%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 5.33 g of 2-acetoxythioacetamide prepared according to Example 2, 5.21 g of 1,3-dichloroacetone, 6.88 g of sodium bicarbonate and 20 ml of 1,2-dichloroethane was stirred at room temperature for 87 hours. The mixture was filtered to remove insoluble inorganics and concentrated under reduced pressure to an oil. The oil was taken up in 4 mls of 1,2-dichloroethane and 25 mls of cyclohexane added dropwise. The slurry was stirred for 1 hour at 0° C. and then filtered. The precipitate was washed with cyclohexane and dried at room temperature under reduced pressure. The product, 2-acetoxymethyl-4-chloromethyl-4-hydroxy-thiazoline was obtained in 92% yield (8.25 g).

Workup

  1. customprepared
  2. filtrationThe mixture was filtered
  3. customto remove insoluble inorganics
  4. concentrationconcentrated under reduced pressure to an oil
  5. addition25 mls of cyclohexane added dropwise
  6. stirringThe slurry was stirred for 1 hour at 0° C.
  7. filtrationfiltered
  8. washThe precipitate was washed with cyclohexane
  9. customdried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-84a7b57dc03e4b0593f80a82f4ebdeea
Source dataset
uspto-grants-1996_07
Patent number
US05541335

Reaction notes

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